Dimethylformamide → HCID 86671898, compound

HRID 83647Notes

Reaction equation

HRID 83647 reaction equation
[H-].[Na+].[CH2:3]([N:10]([CH3:30])[C:11]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN(C=O)C.Br[CH2:37][C:38]#[CH:39]>[Cl-].[NH4+].C(OCC)(=O)C>[CH2:3]([N:10]([CH3:30])[C:11]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([C:21]2[N:22]([CH2:39][C:38]#[CH:37])[C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 66571403N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

Product 1

HCID 86671898HCID 86671898, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

sodium hydride (12.78 mg, 0.320 mmol) was added to an oven dried flask and placed under nitrogen. It was then suspended in 1.0 mL of DMF. The suspension was placed in a 70° C. oil bath before adding N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (100 mg, 0.266 mmol) as a 0.5 mL DMF solution. The reaction was allowed to stir for 20 minutes before the addition of 3-bromoprop-1-yne (0.047 ml, 0.533 mmol) dropwise. The reaction was allowed to stir overnight. The reaction was cooled and diluted with saturated ammonium chloride and ethyl acetate. The organic layer was washed with saturated ammonium chloride followed by saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The yellow crude material was purified via Biotage column 30-70% ethyl acetate:hexanes 4 gram silicycle column to obtain white solid. (Yield: 50 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 7.64-7.53, 7.40-7.05, 6.75-6.65, 5.16-5.04, 4.65, 4.58-3.99, 3.23, 3.10-2.93, 2.76, 1.85-1.52

Workup

  1. customdried flask
  2. customwas placed in a 70° C.
  3. temperatureThe reaction was cooled
  4. washThe organic layer was washed with saturated ammonium chloride
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe yellow crude material was purified via Biotage column 30-70% ethyl acetate
  9. customhexanes 4 gram silicycle column to obtain white solid

Sources & evidence

ORD record
ord-1519c311cd5f45e0a435e8b2ba5b895b
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

Loading…